Guest house holiday rentals in Siena

A charming Tuscan retreat

Villa Pianelli is a traditional farmhouse dating from the 1500's and consists of 2 structures. The main house where I live, always available to ensure your stay runs smoothly and the Garden apartment. Both are completely independant with separate entrances. The Garden apartment is composed of 5 rooms on ground level, the interiors have retained the Tuscan characteristics with brick ceilings and chestnut beams and terracotta floors. There are 2 double bedrooms, 1 bathroom with shower, 1 lounge with a wood burning stove and open plan kitchen - dining area. The kitchen is equipped with fridge,oven and ceramic hob. From the lounge you access the spa room with sauna and from there onto a terraced garden complete with b.b.q. The swimming pool is 8mx16m and is open May through September, furnished with sun loungers,a b.b.q area and a large covered pergola with dining tables and chairs. Villa Pianelli is secluded in a quiet corner of the Tuscan countryside, nestled in the hills of Arezzo, surrounded by vineyards, olive groves and oak forests.We can offer our guests a dimension of peace and quiet whilst ensuring various possibilities of entertainment in wineries, restaurants,shopping etc just a few kilometres away in Arezzo. Please note that the house has two bedrooms but if the booking is for two people only one bedroom will be provided.If required there is an additional cost of 50 euro per night for the second bedroom.

Value · Family · Check-in

Appartment 1 surrounded by Tuscan Nature

This detached appartment has 55 mp with kitchen, bathroom, bedroom, and terrace. It is built in the traditional tuscan style with stone and wood. Its 20 minutes drive to the sea,1 hour to Siena, 2 hours to Rome and Florence, 5 minutes to Caldana city Center where you have all amenities (groceries, bank, Postoffice,3 restaurants..) You will find a lot of activities like horseriding,excursions of history and plants,winetasting and kilometers of wonderfull beaches, watch the birds and wild animals.

Location · Value · Quiet

Top guest favourite

Guest favourite

Tuscan cottage with an heavenly view

Heaven's Window takes your breath away. As our only guests, you will be surrounded by infinite views, endless tranquility, sounds of singing birds and calling deer. Down the valley and on your walks you may spot foxes ferrets and wild boar. Collect porcupine quills. Breathe! Halfway between Rome and Florence. Close to Siena, Val d’Orcia and countless hot springs . A private paradise surrounded by divine dining and hilltop jewels of antiquity like Montepulciano and Montalcino of sublime wines.

Location · Family · Long stay

Cosy apartment with terrace and pool

Set in the beautiful Tuscan countryside in the heart of the famous wine district of Chianti Classico, you find this newly refurbished apartment with private terraces. On the property there is a large pool and gardens. The perfect getaway for those who want to escape, or an ideal base from which to visit Siena, Florence and Arezzo Walking distance of a few hotels, wineries and restaurants. Only a few kilometres away there are the famous Chianti villages; Gaiole, Radda and Castellina.

Location · Biking · Condition

Vacanza a Siena da Simo&Frank

La mia camera si trova in una zona adiacente al centro storico (circa 15 minuti a piedi), distante 1,5 km da Porta Ovile e circa 2 km dalla stazione ferroviaria. L'ingresso è indipendente e il bagno ad uso esclusivo degli ospiti; all'interno di una resede condominiale parcheggio privato per un'auto. A 5 minuti a piedi impianto di risalita di San Francesco per raggiungere agevolmente il centro della città. La posizione tranquilla e riservata è facilmente raggiungibile in auto.

Location · Family · Indoor spaces

La sosta di Alice

La nostra piccola guest-house è perfetta perché situata in un punto strategico della val d’Orcia a 7 km da la località storica e termale di Bagno Vignoni e 8 km dalle terme di Bagni san Filippo, Pienza dista solamente 20km. Circondati da meravigliose camminate e punti panoramici, ottime per passeggiate o per fermate durante il pellegrinaggio. Vicino a noi si trovano attività di noleggio biciclette elettriche oppure se uno preferisce anche una bella passeggiata a cavallo

Location · Condition · Check-in

The Orion Villa

Welcome to Orion at Colle sul Lago. This independent villa on the property boasts 3 bedrooms and 2 full bathrooms (one bedroom is ensuite). There is a large kitchen and an outdoor terrace, both with dining tables. Wake up in true Italian style and enjoy your cappuccino looking out over Lake Montepulciano. Take a stroll through our private forest, or a dip in the beautiful pool. Adventures await as you set off to discover all the magic of Tuscany and Umbria!

Family · Location · View

La Rondine Sea-view Cottage. Tuscany

Welcome to Il Baciarino, a rustic agriturismo in the green hills of Maremma, Tuscany’s wild and less-traveled coastal region. Our property offers unique, handcrafted cottages with sea views, privacy, and direct contact with nature. Set within 19 acres of hillside wilderness in the charming Etruscan town of Vetulonia, Il Baciarino is the perfect place to escape the city, slow down, and enjoy unspoiled landscapes, fresh seafood, and good wine.

Family · Location · Sleep quality

Luxury ground floor apartment La Mangiatoia

Luxe en ruim vierpersoonsappartement in het hart van Toscane. De master bedroom heeft een ligbad en wastafel ensuite. Daarnaast is er een volledige badkamer met douche, toilet en wasbak. Iedere kamer is voorzien van airco en er zijn horren voor ieder raam. Volledig gerenoveerd in 2026. Groot zwembad, een barbecueplek, panoramisch uitzicht en ieder appartement heeft een privéterras buiten. Vlakbij San Gimignano, Certaldo, San Miniato, etc.

Decor · View · Hospitality

Top guest favourite

Guest favourite

LA CASINA: Your tiny house in Tuscany

Cozy cottage rests within garden of architect-restored farmhouse. LA CASINA di Malabiccia is proud to offer year-round hospitality in a unique location amidst the rolling hills of Tuscany. Italian materials and quirky details create an unforgettable charm and comfort. Guests enjoy ample garden space, a fully equipped kitchen and daytrips to Montalcino, Montepulciano, Pienza, Arezzo, Siena, Cortona and more.

Family · Location · Check-in

Secret Haven

The dépendance, fully immersed in the green of the Tuscan countryside, is located in the heart of Valdichiana. The large outdoor spaces and the pool are the ideal place to spend pleasant days among the countryside scents. The house has a double bedroom and a sofa bed in the living room so it can accommodate a maximum of two adults and one child. A baby crib will be made available to guests upon request.

Location · Family · Bathroom

Panoramic loft in crete senesi

The loft, in the characteristic landscape of the Crete Senesi, just 15 km from Siena, 5 km from the main shops and services, is a unique and romantic accommodation. Rebuilt in a ancient barn is totally detached from the main house. Ideal for nature lovers, many paths for walking and mountain biking. Unique view.

Family · Location · Condition